Efficient and convenient synthesis of pyrrolo[1,2-a]quinazoline derivatives with the aid of tin(II) chloride

J Comb Chem. 2010 Jul 12;12(4):582-6. doi: 10.1021/cc100062e.

Abstract

An efficient, convenient, one-pot synthesis of 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one and 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione was accomplished in good yields via the novel reductive cyclization of 2-nitrobenzamides with haloketones or keto acids mediated by SnCl(2).2H(2)O system. A variety of substrates can participate in the process with good yields, making this methodology suitable for library synthesis in drug discovery efforts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Quinazolinones / chemical synthesis*
  • Quinazolinones / chemistry
  • Small Molecule Libraries
  • Stereoisomerism
  • Tin Compounds / chemistry*

Substances

  • Pyrroles
  • Quinazolinones
  • Small Molecule Libraries
  • Tin Compounds
  • stannous chloride